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Diggy Simmons just might be a mogul in the making. At 16 years old he has a budding rap career, and his own sneaker line (Chivalrous Culture) and he’s just getting started. Yup, like his uncle, his hustle is so Russell. Besides being one of the youngest rappers everyone is checking for (follower numbers don't lie), Simmons has always made his fashion sense a priority, and for a young’n has knowledge about kicks that even some the vets don’t. When Diggy stopped by Complex HQ’s a few weeks ago we sat down with him to talk sneakers—something he takes pretty seriously. Check out his top ten of all time, that includes everything from classic Jordans to high-fashion sneakers…

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